diff --git a/rtv/mime_handlers.py b/rtv/mime_handlers.py
new file mode 100644
index 0000000..b5e2dc6
--- /dev/null
+++ b/rtv/mime_handlers.py
@@ -0,0 +1,135 @@
+import re
+import mimetypes
+from html.parser import HTMLParser
+
+import requests
+
+
+class HTMLParsed(Exception):
+    def __init__(self, data):
+        self.data = data
+
+
+class BaseHandler(object):
+    """
+    BaseHandler can be sub-classed to define custom handlers for determining
+    the MIME type of external urls.
+    """
+
+    # URL regex pattern that the handler will be triggered on
+    pattern = re.compile(r'.*$')
+
+    @staticmethod
+    def get_mimetype(url):
+        """
+        Args:
+            url (text): Web url that was linked to by a reddit submission.
+
+        Returns:
+            modified_url (text): The url (or filename) that will be used when
+                constructing the command to run.
+            content_type (text): The mime-type that will be used when
+                constructing the command to run. If the mime-type is unknown,
+                return None and the program will fallback to using the web
+                browser.
+        """
+
+        # Guess based on the file extension
+        filename = url.split('?')[0]
+        content_type, _ = mimetypes.guess_type(filename)
+        return url, content_type
+
+
+class YoutubeHandler(BaseHandler):
+    """
+    Youtube videos can be streamed with vlc or downloaded with youtube-dl.
+    Assign a custom mime-type so they can be referenced in mailcap.
+    """
+
+    pattern = re.compile(
+            r'(?:https?://)?(m\.)?(?:youtu\.be/|(?:www\.)?youtube\.com/watch'
+            r'(?:\.php)?\'?.*v=)([a-zA-Z0-9\-_]+)')
+
+    @staticmethod
+    def get_mimetype(url):
+        return url, 'video/x-youtube'
+
+
+class GifvHandler(BaseHandler):
+    """
+    Special case for .gifv, which is a custom video format for imgur that is
+    incorrectly (or on purpose?) returned with a Content-Type of text/html.
+    """
+    pattern = re.compile(r'.*[.]gifv$')
+
+    @staticmethod
+    def get_mimetype(url):
+        modified_url = url[:-4] + 'webm'
+        return modified_url, 'video/webm'
+
+
+class RedditUploadsHandler(BaseHandler):
+    """
+    Reddit uploads do not have a file extension, but we can grab the mime-type
+    from the page header.
+    """
+    pattern = re.compile(r'https://i.reddituploads.com/.+$')
+
+    @staticmethod
+    def get_mimetype(url):
+        page = requests.head(url)
+        content_type = page.headers.get('Content-Type', '')
+        content_type = content_type.split(';')[0]  # Strip out the encoding
+        return url, content_type
+
+
+class ImgurHTMLParser(HTMLParser):
+    """
+    Scrape the actual image url from an imgur landing page. Imgur intentionally
+    obscures this on most reddit links in order to draw more traffic for their
+    advertisements.
+
+    There are a couple of <meta> tags that supply the relevant info:
+        <meta name="twitter:image" content="https://i.imgur.com/xrqQ4LEh.jpg">
+        <meta property="og:image" content="http://i.imgur.com/xrqQ4LE.jpg?fb">
+        <link rel="image_src" href="http://i.imgur.com/xrqQ4LE.jpg">
+
+    Note:
+        BeautifulSoup or lxml would be faster here but I wanted to skip adding
+        an extra dependency for something as trivial as this.
+    """
+
+    def handle_starttag(self, tag, attr):
+        if tag == 'meta' and attr[0] == ('name', 'twitter:image'):
+            raise HTMLParsed(attr[1][1])
+
+
+class ImgurHandler(BaseHandler):
+    """
+    The majority of imgur links don't point directly to the image, so we need
+    to open the provided url and scrape the page for the link. For galleries,
+    this method only returns the first image.
+    """
+    pattern = re.compile(r'https?://(w+\.)?(m\.)?imgur\.com/[^.]+$')
+
+    @staticmethod
+    def get_mimetype(url):
+        imgur_page = requests.get(url)
+        try:
+            ImgurHTMLParser().feed(imgur_page.text)
+        except HTMLParsed as data:
+            # We found a link
+            url = data.data
+            if GifvHandler.pattern.match(url):
+                return GifvHandler.get_mimetype(url)
+
+        return BaseHandler.get_mimetype(url)
+
+
+# Handlers should be defined in the order they will be checked
+handlers = [
+    ImgurHandler,
+    RedditUploadsHandler,
+    YoutubeHandler,
+    GifvHandler,
+    BaseHandler]